Classifications

• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/40—Table salts; Dietetic salt substitutes
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/204—Aromatic compounds
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/30—Artificial sweetening agents
  • A23L27/33—Artificial sweetening agents containing sugars or derivatives
  • A23L27/37—Halogenated sugars
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/30—Artificial sweetening agents
  • A23L27/39—Addition of sweetness inhibitors

Definitions

• This invention relates in general to bitter taste and sweet taste blockers or inhibitors. More
• the invention relates to the use of substantially tasteless sweetness inhibitors to reduce or block bitter taste and the use of
• Potassium chloride has a
• Lithium chloride although a good tasting salt is highly toxic.
• sweet receptor site and the bitter receptor site are in close proximity and/or related to one another. It is now known, for example, that if sweet molecules are altered
• L-aspartyl L-phenylalanine methyl ester is intensely sweet.
• L-aspartyl L-phenylalanine methyl ester is intensely sweet.
• substantially or essentially tasteless it not only inhibits or reduces the sweetness of substances, but also inhibits or reduces the bitter taste sensation;
• the molecule is a bitter inhibitor and substantially or essentially tasteless, it not only inhibits or reduces the bitter taste of substances, but also inhibits or reduces the sweet taste sensation.
• substantially tasteless are effective bitter taste inhibitors for ingestible substances having a bitter taste characteristic.
• bitterness inhibitors that are substantially tasteless are effective sweetness taste inhibitors for ingestible substances having a bitter taste characteristic.
• these desirable characteristics are not inhibited or adversely affected by the tasteless sweetness inhibitors and/or tasteless bitter
• a certain class of sweetness inhibitors i.e., a certain series of aralkyl carboxylic acid salts, described below, when used in sufficient amounts with mixtures of potassium chloride and sodium chloride or ammonium chloride not only block or inhibit the bitter taste of potassium chloride but also enhance the salty taste of sodium chloride or ammonium chloride.
• sweetness inhibitor as used herein and the appended claims is meant a compound which, when mixed with an ingestible compound or composition naturally possessing or provided with a sweet taste, reduces or eliminates the perceived sweetness.
• sweetness inhibitors of the prior art which are not tasteless can be rendered substantially tasteless by slightly altering the sweetness inhibitor molecule as, for instance, by isomeric molecular reorientation or by the addition or substitution in the inhibitor molecule of various groups.
• Aralkyl carboxylic acid salts having the structure: ⁇ OOC-(CO) m -(CHR) n -(O) q
• m represents 0 or 1, and where m represents 0, n represents 1, 2 or 3 and p represents 1, 2, 3 or 4, and when m represents 1, n represents 1 or 2 and p represents 0, 1, 2, 3 or 4;
• q represents 0 or 1;
• R represents H or a lower alkyl (e.g. of C 1 -C 3
• the substituents R' which may be the same or different, each represents a lower alkoxy group e.g. with 1 to 5 carbon atoms, phenoxy group or a lower alkyl or trifluoromethyl group; and/or two
• substituents R' together represent an aliphatic chain linked to the phenyl ring at two positions, either directly or via an oxa-group, e.g. an alkylenedioxy, alkenylenedioxy, alkylenoxy or alkenylenoxy group; and/or one substituent R' represents a hydroxy group while at least one other substituent R' represents an alkoxy group; and represents a physiologically acceptable cation.
• the in the structure is preferably an alkali metal, alkaline earth metal or ammonium cation. Particularly preferred cations are sodium and potassium.
• the group R' is preferably in the 3- and/or 4-position and is preferably methoxy.
• Sweetness inhibitors of this class have also been found to enhance salt taste.
• effective amounts of these compounds can be used in conjunction with mixtures of bitter substances such as potassium chloride with sodium chloride and/or ammonium
• R 7 is selected from the group consisting of hydrogen and C 1 -C 3 alkyl
• R 3 is selected from
• R 1 is the group consisting of hydrogen and C 1 -C 3 alkyl and wherein R 1 , is the group
• R 2 , R 3 , R 4 , R 5 and R 6 are
• Illustrative members of this class include
• A is COOH; SO 3 H or H; Y is hydroxyl; and R 1 , R 2 and R 3 are H, alkyl from 1 to 3 carbons, cyclo-propyl, OH, OCH 3 , OCH 2 CH 3 , CH 2 OCH 3 , CH 2 CH 2 OH, CH(CH 3 ) CH 2 OH, CHO, COCH 3 , CH 2 CHO, COOH, CH 2 COOH, COOCH 3 , OCOCH 3 , CONH 2 , NHCHO, F, Cl, Br, I, CF 3 , SCH 3 , SCH 2 CH 3 , CH 2 SCH 3 , SO 3 H, SO 2 NH 2 , SOCH 3 , CH 2 SO 3 H and CH 2 S0NH.
• withdrawing group preferably a ureido group, a guanidino group, a urethane group, cyanophenyl group, a nitrophenyl group and the like;
• R' is a group selected from alkyl (e.g. lower alkyl), aryl,
• aralkyl preferably of 6-20 carbon atoms
• Z and Z' are the same or different and are selected from OH, OR'', NH 2 , NHR'', N(R'') 2 ,
• R'' is alkyl, aryl, aralkyl, alkaryl. cycloalkyl, alkyl substituted cycloalkyl (preferably from 4 to 20 carbon atoms) and R''' is H, lower alkyl branched lower alkyl, aryl, aralkyl, alkaryl, or an amino side chain (e.g. one of the 20 common amino acids) attached via an amino group.
• a physiologically acceptable cation preferably an alkali metal, alkaline earth metal or ammonium cation.
• R'' and R''' are alkyl, cycloalkyl, aralkyl, alkaryl and aryl; and is a physiologically
• acceptable cation preferably an alkali metal, alkaline earth metal or ammonium cation.
• R" is CH 3 and R' '' is
• R' and R''' are as hereinbefore defined in the Class "D" compounds above and the physiologically acceptable salts thereof.
• Illustrative of this class of inhibitors are L-methionyl-L-phenylalanine methyl ester L-leucyl-L-phenalalanine methyl ester L-seryl-L-phenylalanine methyl ester L-methionyl-D-alanyl-tetramethyl ⁇ yclopentyl amide
• the class of sweetness inhibitors "A" described above, and in particular, 2-(4-methoxyphenoxy)propionic acid, in addition to inhibiting bitter taste also enhances the salty taste of sodium chloride and ammonium chloride, if employed in sufficient concentrations.
• the present invention contemplates the preparation of ingestible substances containing sodium chloride or ammonium chloride salts and the substantially
• tasteless sweetness inhibitors "A” in an amount sufficient to enhance the salty taste of the sodium chloride or ammonium chloride.
• the present invention contemplates the preparation of ingestible products comprised of a mixture of a substance having a bitter taste such as potassium chloride and sodium or ammonium chlorides in conjunction with the
• substantially tasteless sweetness inhibitors "A” in an amount that both reduces the bitter taste and enhances the salty taste of the sodium or ammonium chlorides.
• Preferred ingestible admixture products of the invention comprise about 50 to 100% by weight of a bitter tasting substance such as potassium chloride and 0 to 50% by weight sodium chloride or ammonium chloride in combination with effective concentrations of sweetness inhibitors "A".
• concentration of sweetness inhibitor employed to reduce the bitter taste in any given instance will vary depending principally on the particular sweetness inhibitor selected, the
• concentrations of about 0.001 to 10% by weight, preferably about 0.05 to 3.5% by weight are satisfactory.
• sweetness inhibitor "A” is selected for use with an admixture of sodium chloride and/or ammonium chloride and a bitter tasting
• neodiosmin having the structure:
• Neodiosmin is a known compound whose preparation and use as a debittering compound is described in U.S. Patent No. 4,154,862.
• ingestible products either naturally sweet or sweetened by the addition of natural sweetening agents can be reduced in sweetness according to the present invention by the addition thereto of
• substantially tasteless bitterness inhibitor In general, this concentration will fall in the range of about 0.001 to 10, preferably 0.05 to 3% by weight.
• the ingestible substances to which the taste inhibitors of the invention can be added are without limitation and include both foodstuff and ingestible substances having essentially no food value such as pharmaceuticals, medicants and other ingestible chemical substances. Therefore, the sweetness inhibitors of the present invention are effective for use with all substances which have a bitter taste, while the bitterness inhibitors can be used with all substances sweetened with natural sugars.
• bitter substances with which the sweetness inhibitors of the invention can be used are potassium chloride, ammonium chloride, naringen, quinine and its salts, caffeine, urea, magnesium sulfate, sodium benzoate, saccharin, acetosulfames, aspirin and the like.
• tasteless bitterness inhibitors of the invention are the various natural sugars and foodstuffs such as beverages, candies, jellies, chocolates, cookies, cakes, sherbets, chewing gum and the like, containing same.
• bitter/metallic after-taste was eliminated from a 0.1% solution of sodium saccharin containing 0.01% 2-(4-methoxyphenoxy)propionic acid.

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• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• Nutrition Science (AREA)
• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Food Science & Technology (AREA)
• Polymers & Plastics (AREA)
• Proteomics, Peptides & Aminoacids (AREA)
• Seasonings (AREA)
• Medicinal Preparation (AREA)
• General Preparation And Processing Of Foods (AREA)
• Peptides Or Proteins (AREA)
• Cosmetics (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Priority Applications (5)

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• 1990
  • 1990-06-01 US US07/531,388 patent/US5232735A/en not_active Expired - Lifetime
• 1991
  • 1991-05-15 ZA ZA913666A patent/ZA913666B/xx unknown
  • 1991-05-17 BR BR919105778A patent/BR9105778A/pt not_active Application Discontinuation
  • 1991-05-17 RU SU915011414A patent/RU2050795C1/ru active
  • 1991-05-17 EP EP96200735A patent/EP0727152A3/de not_active Withdrawn
  • 1991-05-17 DE DE69122473T patent/DE69122473T2/de not_active Expired - Fee Related
  • 1991-05-17 EP EP96200734A patent/EP0728419A3/de not_active Withdrawn
  • 1991-05-17 HU HU9200673A patent/HUT64452A/hu unknown
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  • 1991-05-17 EP EP91911565A patent/EP0485587B1/de not_active Expired - Lifetime
  • 1991-05-17 JP JP3510227A patent/JPH05500756A/ja active Pending
  • 1991-05-17 CA CA2064707A patent/CA2064707A1/en not_active Abandoned
  • 1991-05-17 EP EP96200733A patent/EP0727151A3/de not_active Withdrawn
  • 1991-05-17 AU AU79610/91A patent/AU648804B2/en not_active Ceased
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  • 1991-05-17 AT AT91911565T patent/ATE143569T1/de not_active IP Right Cessation
  • 1991-05-17 KR KR1019920700228A patent/KR920702203A/ko not_active Ceased
  • 1991-05-17 EP EP96200732A patent/EP0727150A3/de not_active Withdrawn
  • 1991-05-17 WO PCT/US1991/003441 patent/WO1991018523A1/en not_active Ceased
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  • 1991-05-29 CS CS911598A patent/CS159891A2/cs unknown
  • 1991-05-29 MY MYPI91000933A patent/MY130080A/en unknown
  • 1991-05-30 EG EG33791A patent/EG19588A/xx active
  • 1991-05-31 YU YU96991A patent/YU47534B/sh unknown
  • 1991-05-31 PT PT97837A patent/PT97837B/pt not_active IP Right Cessation
  • 1991-05-31 IE IE187891A patent/IE911878A1/en not_active Application Discontinuation
  • 1991-06-01 CN CN91103647A patent/CN1029932C/zh not_active Expired - Fee Related

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